Diisobutylaluminumhydride → (S)-tert-butyl 1-methoxybut-3-en-2-yl(2-oxoethyl)carbamate
Reaction equation
CON(C)[C:4](=[O:20])[CH2:5][N:6]([C@@H:14]([CH:18]=[CH2:19])[CH2:15][O:16][CH3:17])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH3:17][O:16][CH2:15][C@@H:14]([N:6]([CH2:5][CH:4]=[O:20])[C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:12])[CH3:10])[CH:18]=[CH2:19]Participants
Procedure
To a solution of (S)-tert-butyl 2-(methoxy(methyl)amino)-2-oxoethyl(1-methoxybut-3-en-2-yl)carbamate (Intermediate 251, 3.35 g, 11.08 mmol) in dichloromethane (60 ml) at −78° C. under nitrogen was added diisobutylaluminum hydride (1.5 eq, 1.0M in dichloromethane) (16.62 ml, 16.62 mmol). The reaction mixture was stirred at that temperature for two hours. The reaction was quenched with slow addition of methanol at the low temperature and slowly warmed to ambient temperature. The reaction mixture was diluted with dichloromethane and washed with 10% aqueous potassium sodium tartrate twice, followed by water and brine. The organics were dried over sodium sulfate, filtered and concentrated. Silica gel chromatography (0%-50% ethyl acetate/hexanes) afforded the title compound as a clear oil (1.8 g, 68%).
Workup
- customThe reaction was quenched with slow addition of methanol at the low temperature
- additionThe reaction mixture was diluted with dichloromethane
- washwashed with 10% aqueous potassium sodium tartrate twice
- dry with materialThe organics were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-aac0c8f7e32b4be7ab66b895248a9894
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309245B2
Reaction notes
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